•However, if your wife or her direct family members receive a financial benefit from the sale (e.g., inheritance distributions from the proceeds), the IRS may consider it a related-party transaction.3.Two-Year Holding Requirement•If the IRS deems this a related-party transaction, you’d need to hold the new property for at least two years before selling or exchanging it again to avoid disqualification.

*As a side note, I think maybe it would be fun also to try and identify where new technology or machine-learning driven approaches could increase efficiency in the spaceAs for my financial situation, personally, I have around 50k saved but 20k of it is tied up in assets I don't want to pay capital gains tax on.

This impressive 7,000 square foot property is situated in an upscale Boston neighborhood.

What is his situation? 

This is rarely done as in most situations lenders will not consent, and at a minimum want the buyer to qualify AND personally guarantee.  

Have an interesting situation, looking for ideas on the best way to solve a problem for a distressed homeowner.

ParkerI find myself in very similar situation in Indiana.

You want to have your financial house in order so you know what you CAN afford and what you SHOULD spend.

If you’re unsure about which specific account to choose, ask a local CPA or banker, since every situation can vary.

I am just surprised it seems Hospitable is the only PMS that has dived into taking on this specific situation.